Dimethylformamide → Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 484485ノート

反応式

HRID 484485 の反応式
[BH4-].[Na+].CN(C)C=O.Cl[C:9](=[O:28])[CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1>O>[OH:28][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 12674069(Phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate

生成物 1

HCID 14989193Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate収率 61.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred and cooled (ice bath, 10° C.) mixture of 3.4 parts of sodium tetrahydroborate and 188 parts of N,N-dimethylformamide were added dropwise 28 parts of (phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate (exothermic reaction, the temperature rose to 38° C.). Upon completion addition, the reaction mixture was stirred over weekend at room temperature. The reaction mixture was poured into water and the product was extracted with methylbenzene. The extract was dried, filtered and evaporated, yielding 15.4 parts (61.6%) of (phenylmethyl) 4-(3-hydroxypropyl)-1-piperidinecarboxylate as a residue (int. 35).

後処理

  1. temperaturecooled
  2. customexothermic reaction
  3. customrose to 38° C.
  4. additionUpon completion addition
  5. stirringthe reaction mixture was stirred over weekend at room temperature
  6. extractionthe product was extracted with methylbenzene
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-e5fbd2d085b84ab38a8b8d7eecf78437
出典データセット
uspto-grants-1993_07
特許番号
US05231184

反応ノート

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