Bicarbonate Ion → 1-Azetidinecarboxylic acid, 3-(1-hydroxy-2-methylpropyl)-, 1,1-dimethylethyl ester

HRID 1945568Notes

Reaction equation

HRID 1945568 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:13][CH:12]([C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(=O)([O-])O>C(O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH:12]([CH:14]([OH:18])[CH:15]([CH3:16])[CH3:17])[CH2:13]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 4311764Sodium borohydrideHCID 59668841HCID 59668841, compound

Product 1

HCID 596053951-Azetidinecarboxylic acid, 3-(1-hydroxy-2-methylpropyl)-, 1,1-dimethylethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (237 mg, 6.26 mmol) was added to a solution of 3-(isobutyryl)azetidine-1-carboxylic acid tert-butyl ester (0.95 g, 4.18 mmol) in ethanol (7.5 mL). The resulting reaction mixture was stirred at RT for 2 h. Saturated hydrogen carbonate (25 mL) was added and the resulting mixture was stirred for further 15 min. The aqueous phase was extracted with dichloromethane (3×25 mL). The organic layer was dried over sodium sulfate and the solvents reduced in vacuo to give the crude product as yellow oil. The residue was purified by column chromatography (Si—PCC, ethyl acetate:cyclohexane: gradient 0:100 to 40:60). The solvents were reduced in vacuo to afford the title compound as colourless oil (840 mg, 88%). 1H NMR (400 MHz, CDCl3): δ 3.91-3.90 (3 H, m), 3.71 (1 H, dd, J=8.54, 6.04 Hz), 3.51 (1 H, dd, J=7.21, 4.97 Hz), 2.70-2.63 (1 H, m), 1.65-1.63 (1 H, m), 1.44 (9 H, s), 0.90 (6 H, t, J=6.59 Hz).

Workup

  1. customThe resulting reaction mixture
  2. stirringthe resulting mixture was stirred for further 15 min
  3. extractionThe aqueous phase was extracted with dichloromethane (3×25 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customto give the crude product as yellow oil
  6. customThe residue was purified by column chromatography (Si—PCC, ethyl acetate:cyclohexane: gradient 0:100 to 40:60)

Sources & evidence

ORD record
ord-62760d6968ea4199a62a23270fdf0a72
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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