(Phenylmethoxy)acetaldehyde → phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylate

HRID 1366640

반응식

HRID 1366640 반응식
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH2:18]([O:25][CH2:26][CH:27]=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:27][CH2:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

참가 물질

5

반응물 3

HCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 40425199Benzyl (2S)-2-methylpiperazine-1-carboxylate

생성물 1

HCID 66935999phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylate수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate (commercially available) (1 g, 4.3 mmol) and benzyloxyacetaldehyde (0.9 mL, 6.4 mmol) in DCM (50 mL) was stirred for 30 minutes, and then NaBH(OAc)3 (1.36 g, 6.4 mmol) was added. The reaction was stirred overnight before being quenched with 1 M NaOH. The phases were separated and the aqueous layer was extracted with DCM. The combined organics were washed with brine, dried over sodium sulfate and concentrated to a crude residue, which was purified by silica gel chromatography (5-95% EtOAc in hexane) yielding phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylate (0.93 g, 58%). LCMS: (M+H)+: 369.1

후처리

  1. custombefore being quenched with 1 M NaOH
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a crude residue, which
  7. customwas purified by silica gel chromatography (5-95% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-ba015d2a15f246e69cfccaecc06d6998
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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