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

HRID 517665

반응식

HRID 517665 반응식
[CH2:1]([O:8][N:9]=[C: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.S(=O)(=O)(O)O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C>[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 3

HCID 1118Sulfuric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 90088575(2S)-5-[(benzyloxy)imino]-2-cyanopiperidine

생성물 1

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

시약·촉매·용매 1

HCID 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-6cc639d5d815446690f58645e01492a5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115131B2

연결된 노트

불러오는 중…