Triethylamine → tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

HRID 500224Notes

Reaction equation

HRID 500224 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([NH:14][C:15]1([C:21](O)=[O:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[BH4-].[Na+]>C1COCC1.O>[C:7]([O:11][C:12](=[O:13])[NH:14][C:15]1([CH2:21][OH:22])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 67114425tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chloroformate (0.234 mL, 0.00245 mol) was added to a solution of 4-[(tert-butoxycarbonyl)amino]tetrahydro-2H-pyran-4-carboxylic acid (0.5 g, 2.0 mmol) and triethylamine (0.341 mL, 2.45 mmol) in THF (6.8 mL) at −10° C. The mixture was stirred at RT for 30 min., filtered, and washed with THF. Sodium tetrahydroborate (0.15 g, 4.1 mmol) in water (1.0 mL) was added to the filtrate at 0° C., and then stirred at RT for 2 h. The reaction mixture was quenched with saturated NH4Cl solution, extracted with EtOAc. The extract was washed with saturated NaHCO3, brine, dried over MgSO4, filtered, and concentrated to give the crude product which was directly used in next step without further purification. LCMS: (M+Na)=254.1; (M−100+H)=132.1.

Workup

  1. filtrationfiltered
  2. washwashed with THF
  3. stirringstirred at RT for 2 h
  4. customThe reaction mixture was quenched with saturated NH4Cl solution
  5. extractionextracted with EtOAc
  6. washThe extract was washed with saturated NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cd519210ea6f4e84947ec7266cf72037
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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