(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate → (S)-tert-Butyl 2-(phenoxymethyl)azetidine-1-carboxylate

HRID 2191229Notes

Reaction equation

HRID 2191229 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:13]C[CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(OC[C@@H]2CCN2C(OC(C)(C)C)=O)(=O)=O)=CC=1>>[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylateHCID 11602568(S)-tert-Butyl 2-((tosyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 11565179(S)-tert-Butyl 2-(phenoxymethyl)azetidine-1-carboxylateYield 79%

Procedure

(S)-tert-Butyl 2-(phenoxymethyl)azetidine-1-carboxylate (16) was prepared according to the same procedure for compound 9, except using compound 15, and purified with hexanes-ether (2:1) to afford 0.81 g (79%) of 16 as a colorless oil. 1H NMR (300 MHz, CDCl3) δ CDCl3 7.30 (m, 2H), 6.94 (m, 3H), 4.53 (m, 1H), 4.26 (m, 1H), 4.12 (m, 1H), 3.93 (m, 2H), 2.33 (m, 2H), 1.43 (s, 9H).

Workup

  1. custom(S)-tert-Butyl 2-(phenoxymethyl)azetidine-1-carboxylate (16) was prepared
  2. custompurified with hexanes-ether (2:1)

Sources & evidence

ORD record
ord-687d2629b79e49d895b356b5cee81d8f
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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