Sodium Hydroxide → Tert-butyl 4-(aminomethyl)-4-(cyclopropylmethyl)piperidine-1-carboxylate

HRID 551140노트

반응식

HRID 551140 반응식
[C:1]([C:3]1([CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[OH-].[Na+]>C(O)C.C(O)C.O>[NH2:2][CH2:1][C:3]1([CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:5][CH2:4]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 57425738Tert-butyl 4-cyano-4-(cyclopropylmethyl)piperidine-1-carboxylate

생성물 1

HCID 57425745Tert-butyl 4-(aminomethyl)-4-(cyclopropylmethyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 19096565Water ethanol용매

실험 절차

A solution of the tert-butyl 4-cyano-4-cyclopropylmethylpiperidine-1-carboxylate (I-2) (1.00 g, 3.78 mmol) in ethanol (5 mL) was added to 1M sodium hydroxide in 95% ethanol-water (75 mL) and the solution degassed with nitrogen. Raney Nickel (50% slurry in water) (2.6 g) was added and the black suspension shaken under hydrogen pressure (40 psi) at room temperature for 12 h. The catalyst was filtered off and washed with 95% ethanol-water. The filtrate was evaporated in vacuo then partitioned between water and DCM. The organic phase was separated and the aqueous phase re-extracted with DCM twice. The combined organic phase was dried (MgSO4) and the solvent removed in vacuo to leave tert-butyl 4-aminomethyl-4-cyclopropylmethylpiperidine-1-carboxylate (I-3) that was used in the next step without further purification. 1H NMR (500 MHz, CDCl3): δ 3.44 (m, 2H), 3.32 (m, 2H), 2.71 (s, 2H), 1.41 (s, 9H), 1.46-1.38 (m, 4H), 1.28 (d, J=6.7, 2H), 1.46 (s, 9H), 0.60 (m, 1H), 0.46 (m, 2H), 0.05 (m, 2H).

후처리

  1. customthe solution degassed with nitrogen
  2. additionRaney Nickel (50% slurry in water) (2.6 g) was added
  3. filtrationThe catalyst was filtered off
  4. washwashed with 95% ethanol-water
  5. customThe filtrate was evaporated in vacuo
  6. customthen partitioned between water and DCM
  7. customThe organic phase was separated
  8. extractionthe aqueous phase re-extracted with DCM twice
  9. dry with materialThe combined organic phase was dried (MgSO4)
  10. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-1ecdf9b7949546eaac52e0bc34f55085
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947714B2

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