Triethylamine → 1,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

HRID 1869623노트

반응식

HRID 1869623 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[C:21]1(=O)[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:21]1([N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]3[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]3)[CH2:5][CH2:6]2)[CH2:24][CH2:23][CH2:22]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

생성물 1

HCID 688866201,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (4.8 g), cyclobutanone (3.81 ml) and triethylamine (4.7 ml) were stirred in DCM (200 ml) at room temperature. After 10 min sodium triacetoxyborohydride (7.2 g) was added and the reaction was stirred at room temperature overnight. The reaction mixture was evaporated and redissolved in dichloromethane (50 ml). After washing with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml) the organic phase was dried (MgSO4) and evaporated to give the title compound (D5) as a colourless solid (5.72 g).

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionredissolved in dichloromethane (50 ml)
  3. washAfter washing with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml) the organic phase
  4. dry with materialwas dried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-077f1b4d6a6c4af9b54980b4a66a9fc8
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638631B2

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