Ammonia → tert-butyl (2S,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 82770Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].N>>[F:13][C@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@H:9]([CH2:14][OH:15])[CH2:10]1

Participants

Reactant 2

HCID 222Ammonia

HCID 2756017(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Product 1

HCID 67092752tert-butyl (2S,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Procedure

The title compound was prepared as described in Example 53A substituting (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid for (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid. MS (DCI/NH3) m/z 220 (M+H)+.

Sources & evidence

ORD record: ord-7f3bc86191574f4e9bab7596a51946d1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846730B2

Reaction notes

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