tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate → tert-Butyl (R)-3-phenoxypyrrolidine-1-carboxylate

HRID 341555Notes

Reaction equation

HRID 341555 reaction equation
O[C@H]1CCN(C(OC(C)(C)C)=O)C1.[O:14]([C@H:21]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[O:14]([C@@H:21]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 69333485(S)-Tert-Butyl 3-phenoxypyrrolidine-1-carboxylate

Product 1

HCID 86610018tert-Butyl (R)-3-phenoxypyrrolidine-1-carboxylateYield 51%

Procedure

tert-Butyl (3R)-3-phenoxypyrrolidine-1-carboxylate was prepared from tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (0.43 g, 2.286 mmol) according to the method described for Intermediate 270 to afford the title compound (0.312 g, 51% yield). Method B HPLC-MS: MH+ requires m/z=208 Found: m/z=208, Rt=2.20 min (100%).

Sources & evidence

ORD record
ord-ee7c04f87cd04381a9f4d7418bc9e29b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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