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

HRID 1257880노트

반응식

HRID 1257880 반응식
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>[OH:22][CH2:21][C:15]1([NH:14][C:12](=[O:13])[O:11][C:7]([CH3:9])([CH3:8])[CH3:10])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-af401de686364cd88517f50cc46b8387
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461330B2

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