4-Methylmorpholine → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

HRID 2269645Notes

Reaction equation

HRID 2269645 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6](O)=[O:7])[CH:3]([CH3:5])[CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O>COCCOC>[C:9]([NH:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:4])[CH3:5])([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 83693Boc-L-Valine

Product 1

HCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamateYield 86.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In 5 ml of 1,2-dimethoxyethane (DME), 1.086 g of Boc-Val-OH was dissolved and 550 μl of N-methylmorpholine and 650 μl of isobutyl chloroformate were successively added dropwise at −15° C. After stirring for 1 min, N-methylmorpholine hydrochloride was filtered off and washed twice with 2.5 ml each of DME. The filtrate and washings were combined and a solution of 284 mg of sodium borohydride in 2.5 ml of water was added in one portion. After 30 sec, 125 ml of water was added and the mixture was extracted with 25 ml of ethyl acetate and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure to give 879 mg of the title compound.

Workup

  1. filtrationN-methylmorpholine hydrochloride was filtered off
  2. washwashed twice with 2.5 ml each of DME
  3. additiona solution of 284 mg of sodium borohydride in 2.5 ml of water was added in one portion
  4. waitAfter 30 sec
  5. addition125 ml of water was added
  6. extractionthe mixture was extracted with 25 ml of ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe dried solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5373fadc27ee44669e77b70e453ce314
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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