Sodium borohydride → HCID 66856859, compound

HRID 2037617Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([N:11]2[CH2:16][CH2:15][C:14]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)([CH3:17])[O:13][C:12]2=[O:26])[CH3:10])=[CH:5][CH:4]=1.[BH4-].[Na+]>>[OH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([C@:14]2([CH3:17])[O:13][C:12](=[O:26])[N:11]([C@H:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH3:10])[CH2:16][CH2:15]2)=[CH:19][CH:20]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 86649950HCID 86649950, compound

Product 1

HCID 66856859HCID 66856859, compound

Procedure

Reaction of 4-(3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-2-oxo-1,3-oxazinan-6-yl)benzaldehyde isomer 1 with NaBH4, under conditions analogous to those described above for isomer 2, afforded (R)-6-(4-(hydroxymethyl)phenyl)-3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-1,3-oxazinan-2-one. LC-MS Method 1 tR=1.39 min, m/z=356 (M+1); 1H NMR (CD3OD) 7.27 (d, J=8.5 Hz, 2H), 7.21 (d, J=8.5 Hz, 2H), 6.78 (d, J=8.8 Hz, 2H), 6.59 (d, J=8.8 Hz, 2H), 5.41 (q, J=7.0 Hz, 1H), 4.53 (s, 2H), 3.62 (s, 3H), 2.96-2.91 (m, 1H), 2.37-2.32 (m, 1H), 2.22-2.15 (m, 1H), 2.10-2.02 (m, 1H), 1.51 (s, 3H), 1.41 (d, J=7.0 Hz, 3H).

Sources & evidence

ORD record: ord-48c5aadd5a24489a8d219d0dfcc24a8c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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