Sodium borohydride → HCID 86602902, compound

HRID 2252501Notes

Reaction equation

HRID 2252501 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:35]([CH3:82])/[CH:36]=[CH:37]\[C@@H:38]([O:74][Si:75]([C:78]([CH3:81])([CH3:80])[CH3:79])([CH3:77])[CH3:76])[CH2:39][C@H:40]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[C@H:41]([CH3:65])/[CH:42]=[CH:43]/[CH2:44][O:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C@@H:10]([CH3:34])[CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15](=[O:33])[C@@H:16]([C@@H:18]1[C@@H:23]([CH3:24])[CH2:22][O:21][CH:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[O:19]1)[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CCOC(C)=O.CCCCCC>[Si:1]([O:8][C@@H:9]([C@@H:35]([CH3:82])/[CH:36]=[CH:37]\[C@@H:38]([O:74][Si:75]([C:78]([CH3:81])([CH3:80])[CH3:79])([CH3:77])[CH3:76])[CH2:39][C@H:40]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:68])[CH3:69])[C@H:41]([CH3:65])/[CH:42]=[CH:43]/[CH2:44][O:45][C:46]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C@@H:10]([CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:33])[C@@H:16]([C@@H:18]1[C@@H:23]([CH3:24])[CH2:22][O:21][CH:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[O:19]1)[CH3:17])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86602903HCID 86602903, compound

Product 1

HCID 86602902HCID 86602902, compoundYield 65,417.199%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The procedure for 40 was used with 69 (1.22 g, 1.04 μmol), NiCl2.6H2O (0.12 g, 0.52 mmol) and NaBH4 (0.079 g, 2.08 mmol) to yield 70 (0.80 g, 65%) after flash column chromatography (EtOAc/hexane 1:9) as a colorless oil: IR (CHCl3) 2956, 2929, 2855, 1713, 1615, 1518, 1461, 1388, 1251, 1077, 1037, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.70-7.66 (m, 6H), 7.57-7.40 (m, 1H), 7.07-7.04 (m, 2H), 5.92-5.77 (m, 2H), 5.65 (m, 1H), 5.64 (s, 1H), 5.52 (m, 1H), 4.78 (m, 1H), 4.30 (dd, J=11.2, 4.6 Hz, 1H), 4.14 (m, 2H), 3.94 (s, 3H), 3.79 (d, J=3.9 Hz, 2H), 3.73 (t, J=11.1 Hz, 1H), 3.61 (m, 1H), 2.92-2.79 (m, 2H), 2.72 (t, J=7.4 Hz, 2H), 2.65 (m, 1H), 2.22 (m, 1H), 1.91-1.71 (m, 4H), 1.65-1.56 (m, 3H), 1.51 (m, 1H), 1.43 (d, J=7.1 Hz, 3H), 1.35 (m, 1H), 1.20 (d, J=6.7 Hz, 3H), 1.14-1.12 (m, 21H), 1.08 (d, J=6.2 Hz, 3H), 1.05-1.03 (m, 9H), 0.96 (d, J=6.7 Hz, 3H), 0.34-0.25 (m, 18H); 13C NMR (75 MHz, CDCl3) 6 211.5, 159.8, 144.4, 144.3, 134.3, 132.9, 132.2, 130.9, 128.6, 127.6, 127.1, 126.8, 113.4, 100.8, 86.7, 83.0, 80.1, 72.8, 72.2, 66.4, 65.0, 55.0, 48.2, 42.3, 41.6, 40.6, 38.0, 35.7, 33.5, 31.2, 27.6, 26.2, 25.91, 25.87, 23.9, 19.4, 18.4, 18.05, 17.99, 14.8, 13.2, 12.0, 9.5, −3.0, −3.6, −3.8, −4.2, −4.3, −4.4; LRMS (ESI) 1197.7 [M+Na]+, 684.2, 541.1; HRMS (ESI) calcd for C71H110O8Si3Na 1197.7406 [M+Na]+, found 1197.7411; [α]20D+4.6 (c 1.1, CHCl3).

Sources & evidence

ORD record
ord-acf1933bbd3b4f79be24e7cb3f8f1fa1
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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