Formaldehyde → HCID 66980534、化合物

HRID 1038801

反応式

HRID 1038801 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 66980534HCID 66980534、化合物収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5c54e5ae32254843bbadc584dacfc6c3
出典データセット
uspto-grants-2013_10
特許番号
US08551981B2

関連ノート

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