3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → HCID 59605396, compound

HRID 1945511Notes

Reaction equation

HRID 1945511 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[C:7]([O:11][C:12]([N:14]1[CH2:17][C:16](=O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([N:1]2[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 2733874(3S)-pyrrolidin-3-olHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59605396HCID 59605396, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (S)-pyrrolidin-3-ol (261 mg, 3.0 mmol), 3-oxoazetidine-1-carboxylic acid tert-butyl ester (513 mg, 3.0 mmol) and 4 Å powdered molecular sieves (1.0 g) in DCE (10 mL) was stirred at room temperature for 6 h before the addition of sodium triacetoxyborohydride (1.27 g, 6.0 mmol). The reaction mixture was filtered through celite, washing with DCM. The filtrate was concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, Acetone:DCM, 0-40%) affording 3-((S)-3-Hydroxypyrrolidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester as a brown oil (390 mg, 54%). LCMS (Method A): RT 0.28 min [M+H]+ 243.0

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashing with DCM
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting residue was purified by column chromatography (Si—PCC, Acetone:DCM, 0-40%)

Sources & evidence

ORD record
ord-bff1e800502e40f0b5c8ca4c65379a01
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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