Ammonium Chloride → HCID 86604507, 화합물

HRID 1858829노트

반응식

HRID 1858829 반응식
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:4]1[OH:16])#[N:2].C(C1C(O)CCN(C(OC(C)(C)C)=O)C1)#N.O.[SH2:34].[Na].[Cl-].[NH4+]>CN(C)C=O>[OH:16][CH:4]1[CH:3]([C:1](=[S:34])[NH2:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5]1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 53442613Sodium hydrogen sulfide hydrateHCID 54013516HCID 54013516, 화합물HCID 83670143HCID 83670143, 화합물

생성물 1

HCID 86604507HCID 86604507, 화합물수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5.8 g (25.6 mmol) of a 4:1 mixture of tert-butyl (3RS,4RS)-4-cyano-3-hydroxy-piperidine-1-carboxylate and tert-butyl (3RS,4SR)-3-cyano-4-hydroxy-piperidine-1-carboxylate in 50 ml of N,N-dimethylformamide was stirred at room temperature under argon for 4 hours with 1.8 g (38.4 mmol) of sodium hydrogen sulphide monohydrate and 2.05 g (38.4 mmol) of ammonium chloride. For the working-up, the reaction mixture was evaporated under reduced pressure and the residue was taken up in 150 ml of methylene chloride. The solution obtained was washed twice with 10 ml of water each time and the organic phase was separated, dried over sodium sulphate and then evaporated under reduced pressure. For purification and separation of the isomer mixture, the residue was chromatographed on silica gel using a 95:5:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 3.48 g (52% of theory) of tert-butyl (3RS,4SR)-3-hydroxy-4-thiocarbamoyl-piperidine-1-carboxylate, (Rf : 0.37, silica gel; methylene chloride:methanol:ammonia=90:10:0.1 v/v/v), MS: 260 (M)+, as well as 1.2 g of a mixture of tert-butyl (3RS,4SR)-3-hydroxy-4-thiocarbamoyl-piperidine-1-carboxylate and tert-butyl (3RS,4RS)-4-hydroxy-3-thiocarbamoyl-piperidine-1-carboxylate, each as a colourless oil.

후처리

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customThe solution obtained
  3. washwas washed twice with 10 ml of water each time
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customFor purification and separation of the isomer mixture
  8. customthe residue was chromatographed on silica gel using
  9. additiona 95:5:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

출처 및 근거

ORD 기록
ord-971fbe5870e6496e9baf09d338ff9c82
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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