Hydrochloric Acid → 4-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

HRID 916324노트

반응식

HRID 916324 반응식
O=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+].[ClH:31]>CO>[ClH:31].[NH2:28][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile

생성물 1

HCID 1317266004-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride수율 36%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

156AF03-217 (252 mg, 0.912 mmol) was dissolved in methanol (25 mL). Ammonium acetate (702 mg, 9.12 mmol) and sodium cyanoborohydride (57.3 mg, 0.912 mmol) were added together with some molecular sieves (3 Å). This mixture was allowed to react at rt for 60 hours. Hydrochloric acid (2 M) was added until pH<2 and the mixture was washed with ethyl acetate (2×25 mL). The aqueous layer was made alkaline with sodium hydroxide and extracted with ethyl acetate (3×30 mL). The combined organic layers were evaporated to dryness and purified by ion-exchange (SCX) to give 90 mg (36%) of the title compound.

후처리

  1. customto react at rt for 60 hours
  2. washthe mixture was washed with ethyl acetate (2×25 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. customThe combined organic layers were evaporated to dryness
  5. custompurified by ion-exchange (SCX)

출처 및 근거

ORD 기록
ord-20ff5d02b7bd41fcaab39fc58b6fde2c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268232B2

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