Hydrochloric Acid → 4-{[(2S)-2-Hydroxy-3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]-oxy}benzonitrile

HRID 411134노트

반응식

HRID 411134 반응식
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C@@H:9]([OH:27])[CH2:10][N:11]2[CH2:18][CH:17]3[O:19][CH:13]([CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH:27][C@@H:9]([CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][NH:15][CH2:16]2)[CH2:12]1)[CH2:8][O:7][C:6]1[CH:28]=[CH:29][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 21076121tert-Butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

생성물 1

HCID 684578084-{[(2S)-2-Hydroxy-3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]-oxy}benzonitrile수율 91%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of tert-butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (ii) above; 1.0 g, 2.47 mmol) in ethyl acetate (13 mL) was cooled to 0° C. Ethyl acetate (26 mL) saturated with gaseous HCl was added, and the mixture stirred for 4 h at rt. The solvent was removed in vacuo before MeCN (25 mL), water (1.3 mL) and K2CO3 (2.0 g) were added. The resulting mixture was stirred overnight before CHCl3 was added, and the mixture filtered through Celite®. The filtrate was concentrated in vacuo to give 682 mg (91%) of the title compound.

후처리

  1. customThe solvent was removed in vacuo before MeCN (25 mL), water (1.3 mL) and K2CO3 (2.0 g)
  2. additionwere added
  3. stirringThe resulting mixture was stirred overnight before CHCl3
  4. additionwas added
  5. filtrationthe mixture filtered through Celite®
  6. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-d64d31dc68a54d98b015387833b5ff27
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559143B1

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