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

HRID 484485노트

반응식

HRID 484485 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e5fbd2d085b84ab38a8b8d7eecf78437
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231184

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