Oxalic Acid → (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

HRID 517666

반응식

HRID 517666 반응식
[CH2:1]([O:8][NH:9][CH:10]1[CH2:15][NH:14][C@H:13]([C:16]#[N:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20]>C(OC(=O)C)C.CC(C)=O>[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20].[CH2:1]([O:8][NH:9][CH:10]1[CH2:15][NH:14][C@H:13]([C:16]#[N:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 971Oxalic AcidHCID 117599345(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine

생성물 1

HCID 131732538(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

The compound of Formula (IX) was reacted with sulphuric acid and sodium triacetoxy borohydride, in presence of suitable solvent such as ethyl acetate and at temperature below −5° C., to provide (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine (X). The compound of Formula (X) was purified by forming oxalate salt. The compound of Formula (X) was reacted with oxalic acid in a mixture of ethylacetate and acetone to provide (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate (1:1) (XI), which was further treated with sodium hydrogen carbonate to obtain purified (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine (XII). The racemic compound (XI) was treated with methanol to obtain pure (2S,5R)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate.

출처 및 근거

ORD 기록
ord-74a80cbeac854130a1df403569ddc284
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115131B2

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