Hydrochloric Acid → Hydrate;hydrochloride

HRID 1511853노트

반응식

HRID 1511853 반응식
[NH2:1][C@:2]1([C:21](OC)=[O:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[BH4-].[Na+].[ClH:27]>CCO>[NH2:1][C@:2]1([CH2:21][OH:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[OH2:19].[ClH:27]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57554704(1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate

생성물 2

HCID 21885828Hydrate;hydrochlorideHCID 25001810((1R,3R)-1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentyl)methanol

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate (12.84 g, 38.5 mmol) in EtOH (50 mL) was added dropwise to a solution of sodium borohydride (4.37 g, 115 mmol) in EtOH (50 mL). After about 15 hours 2N HCl was added slowly to the reaction mixture. The mixture was partially concentrated in vacuo and partitioned between EtOAc and water. The organic layer was separated and the solvent was removed in vacuo and the residue was dissolved in warm dioxane (100 mL) and water (1 mL) after cooling to about room temperature. The resulting solid was collected by filtration and dried in vacuo to provide ((1R,3R)-1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentyl)methanol, hydrochloric acid, monohydrate.

후처리

  1. concentrationThe mixture was partially concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. customthe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in warm dioxane (100 mL)
  6. temperaturewater (1 mL) after cooling to about room temperature
  7. filtrationThe resulting solid was collected by filtration
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-3b8a2d847be54882ae328e47c6508082
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217027B2

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