Methanol → (S)-1-(4-benzylpiperazin-1-yl)-2-hydroxypropan-1-one

HRID 341311노트

반응식

HRID 341311 반응식
[OH:1][C@@H:2]([CH3:11])[C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].O[C@@H](C)C(OCC)=O.[CH2:20](N1CCNCC1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO>C[O-].[Na+]>[CH2:20]([N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C@@H:2]([OH:1])[CH3:11])[CH2:10][CH2:9]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 759941-BenzylpiperazineHCID 92831(L)-ethyl lactateHCID 68437343(S)-2-hydroxy-1-(piperazin-1-yl)propan-1-one

생성물 1

HCID 58046370(S)-1-(4-benzylpiperazin-1-yl)-2-hydroxypropan-1-one

시약·촉매·용매 1

HCID 10942334Sodium Methoxide용매

실험 절차

Scheme 4 shows the synthesis of intermediate (S)-2-hydroxy-1-(piperazin-1-yl)propan-1-one V from (S)-ethyl 2-hydroxypropanoate 7. 1-Benzylpiperazine and 7 were reacted in sodium methoxide and methanol to give (S)-1-(4-benzylpiperazin-1-yl)-2-hydroxypropan-1-one 8, isolated from AMBERLITE® IRC-748 resin or oxalic acid, followed by the activated charcoal treatment (Example 10). Reductive cleavage removal of the benzyl group from 8 was effected by palladium catalysis with either hydrogen gas (Method A) or cyclohexene (Method B) to give intermediate (S)-2-hydroxy-1-(piperazin-1-yl)propan-1-one 6 (Example 11). The oxalate salt was formed from 6 with oxalic acid in ethanol and tetrahydrofuran to give V (Example 11).

출처 및 근거

ORD 기록
ord-8a344c21fda143c1b2ec14a74bab56b2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895729B2

반응 노트

불러오는 중…