Potassium Carbonate → tert-butyl N-(2-oxocyclopentyl)carbamate

HRID 245052

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HRID 245052 반응식
[Br-].[K+].[OH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].Cl[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Cl-].[Na+].CC1(C)CCCC(C)(C)[NH+]1[O-]>[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 23665760Sodium HypochloriteHCID 45091953(1R,2R)-trans-N-Boc-2-Aminocyclopentanol

생성물 1

HCID 357962tert-butyl N-(2-oxocyclopentyl)carbamate수율 76.3%

시약·촉매·용매 3

HCID 101250832,2,6,6-Tetramethyl-piperidine 1-oxide촉매HCID 5234Sodium Chloride용매HCID 6344Dichloromethane용매

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온도
5 °C

실험 절차

2,2,6,6-Tetramethylpiperidine-N-oxide (2.2 g, 14.2 mmol) and potassium bromide (8.5 g, 71 mmol) are added to a solution of racemic trans-tert-butyl N-[2-hydroxycyclopentyl]carbamate (75 g, 283 mmol) in dichloromethane (285 mL). The mixture is cooled to 5° C. with stirring. A freshly prepared ice cooled (5° C.) sodium hypochlorite aqueous solution (766 mL, 566 mmol, pH adjusted to 7.5-8 by addition of 10 g of solid potassium carbonate) is added with stirring to the reaction mixture while keeping the temperature below 5° C. The mixture is stirred at 5° C. for an additional 30 min. The reaction mixture is diluted with saturated aqueous sodium chloride solution (150 mL). The organic layer is separated and evaporated. The oily red residue is purified over a silica gel pad, eluting with EtOAc/hexanes (1/3) to obtain the title compound as a cream colored solid (43 g, 76%). 1H-NMR (300 MHz, DMSO-d6) δ 6.99 (d, 1H, NH), 3.76 (q, 1H), 1.63-2.31 (m, 6H), 1.37 (s, 9H).

후처리

  1. additionis added
  2. stirringwith stirring to the reaction mixture
  3. customthe temperature below 5° C
  4. stirringThe mixture is stirred at 5° C. for an additional 30 min
  5. customThe organic layer is separated
  6. customevaporated
  7. customThe oily red residue is purified over a silica gel pad
  8. washeluting with EtOAc/hexanes (1/3)

출처 및 근거

ORD 기록
ord-168dca8190654a0589aeb29b2d568a89
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658693B2

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