(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine → HCID 21034348, compound

HRID 1830981Notes

Reaction equation

HRID 1830981 reaction equation
[OH:1][C@H:2]1[C@@H:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:6](=[O:12])[C:5]2[CH:13]=[CH:14][CH:15]=[C:16](OC)[C:4]=2[N:3]1[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].C(OC([N:33]1C[C@H](O)C[C@H]1CO[Si](C(C)(C)C)(C)C)=O)C=C>C(Cl)(Cl)Cl>[NH2:33][C:15]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[N:7]3[CH2:11][CH2:10][CH2:9][C@H:8]3[C@H:2]([OH:1])[N:3]([C:19]([O:21][CH2:22][C:23]([Cl:24])([Cl:26])[Cl:25])=[O:20])[C:4]=2[CH:16]=1

Participants

4

Reactant 2

HCID 18639173(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine2×HCID 86588596HCID 86588596, compound

Product 1

HCID 21034348HCID 21034348, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The protected carbinolamine 149 (0.8 g, 1.3 mmol) was added to a 5% solution of piperidine in CH3CN (12 mL, 5 eq. of piperidine). The mixture was allowed to stir for 12 hours, extracted with water (2×50 mL) and the organic phase was evaporated under reduced pressure to yield a pale yellow oil (0.24 g, 50%): 1H NMR (270 MHz, CDCl3) δ1.9-2.2 (m, 4H); 3.45-3.7 (m, 3H); 4.26 (d, J=12.1 Hz, 1H); 4.55 (m, 3H); 5.18 (d, J=12.1 Hz, 1H); 5.61 (d, J=10.3 Hz, 1H); 6.61 (s, 1H); 6.69 (d, J=7.3 Hz, 1H); 7.56 (d, J=8.2 Hz, 1H). 13C NMR (67.8 MHz, CDCl3) δ23.0; 28.7; 46.3; 59.8; 74.9; 95.1; 114.8; 116.5; 130.4; 135.3; 154.4; 167.3. IR (Nujol): cm−1 3340, 3224, 3000-2800, 1714, 1602, 1460, 1311, 1208, 1141, 1061, 826, 759, 665. MS: m/e (relative intensity) 407 (M+. , 40), 381 (5), 340 (10), 309 (25), 161 (100), 134 (15), 105 (15), 70 (80). HRMS Calculated for C15H16C13N3O4. 407.0206. Found: 407.0206. [α]25D=+47.8° (c=0.5, CHCl3).

Sources & evidence

ORD record
ord-11cb4923d44d48859e70a444dea8c191
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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