Dimethyl Sulfide → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1434865Notes

Reaction equation

S(C)C.[C:4]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15](O)=[O:16])[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>>[C:4]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH2:15][OH:16])[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 2

HCID 1068Dimethyl Sulfide

HCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Procedure

Using a procedure analogous to Example 40-B (using Me2S.BH3), 1-t-butoxycarbonylazetidine-3-carboxylic acid gave the title compound (3.0 g, quantitative).

Sources & evidence

ORD record: ord-92a2b9c190684355b64238e4614ffc59
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615568B2

Reaction notes

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