Water → (2S,4S)-4-Aminomethyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

HRID 1527398Notes

Reaction equation

HRID 1527398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+]=[N-])([F:13])[CH2:10][C@H:9]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].CP(C)C.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][NH2:15])([F:13])[CH2:10][C@H:9]1[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86673843HCID 86673843, compound

Product 1

HCID 68284280(2S,4S)-4-Aminomethyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2S,4R)-4-azidomethyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (prepared as described in Scheme B16) (1 g, 2.64 mmol), trimethylphosphine in THF (3.17 mL, 3.17 mmol) and water (0.10 mL, 5.29 mmol) in THF (40 mL) was stirred for 16 h at RT. The reaction mixture was quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 9:1). MS (UPLC/MS): 353 [M+H]+, 411 [M+HCOO]−; tR (HPLC conditions f): 1.62 min.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 9:1)
  8. custom1.62 min.

Sources & evidence

ORD record
ord-4cd9d3f5b5ac439ea02e71e287070b32
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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