Formaldehyde → HCID 66980534, 화합물

HRID 1038801

반응식

HRID 1038801 반응식
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:29]=[O:30]>C1COCC1>[C:1]([C:3]1([CH2:29][OH:30])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

생성물 1

HCID 66980534HCID 66980534, 화합물수율 41%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of benzyl 4-cyanopiperidine-1-carboxylate (1.0 g, 4.0 mmol, Oakwood) in THF (50 mL) at about −78° C. was added LiHMDS (1.0 M solution in THF, 6.14 mL, 6.14 mmol) dropwise via syringe. The mixture was stirred for about 1 h. Paraformaldehyde (0.25 g, 8.2 mmol) was added in one portion and the mixture was stirred overnight at rt. The mixture was concentrated in vacuo and the residue was purified by preparative TLC (1:1 EtOAc/pet ether) to give benzyl 4-cyano-4-(hydroxymethyl)piperidine-1-carboxylate (0.45 g, 35%): LC/MS (Table 2, Method k) Rt=0.60 min; MS m/z: 274 (M+H)+.

후처리

  1. stirringthe mixture was stirred overnight at rt
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by preparative TLC (1:1 EtOAc/pet ether)

출처 및 근거

ORD 기록
ord-5c54e5ae32254843bbadc584dacfc6c3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551981B2

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