Sodium triacetoxyborohydride → (9-(2-(4-(2-Hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 1689190노트

반응식

HRID 1689190 반응식
Cl.[CH3:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([N:10]2[CH2:15][C:14]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[O:13][CH2:12][CH2:11]2)=[O:9])[N:7]=1.[OH:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH:30]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.CO>[OH:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH2:30][N:18]2[CH2:19][CH2:20][C:14]3([O:13][CH2:12][CH2:11][N:10]([C:8]([C:6]4[N:7]=[C:3]([CH3:2])[S:4][CH:5]=4)=[O:9])[CH2:15]3)[CH2:16][CH2:17]2)=[CH:26][CH:25]=1

참가 물질

7

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 545162782-(4-(2-Hydroxyethyl)phenoxy)acetaldehydeHCID 67291637(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride

생성물 1

HCID 57988908(9-(2-(4-(2-Hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride (example 1, step f) (0.63 g) was added to a solution of 2-(4-(2-hydroxyethyl)phenoxy)acetaldehyde (example 3, step b) (0.541 g) in a mixture of NMP (10 mL) and acetic acid (0.11 mL). The resulting mixture was stirred at room temperature for 30 min then cooled in an ice bath. Sodium triacetoxyborohydride (0.64 g) was then added and the reaction was allowed to warm to room temperature and stirred for 16 h. The reaction was diluted with methanol (30 mL) and applied to a SCX cartridge pre-wetted with methanol. The cartridge was washed with methanol (100 mL) and eluted with 3M ammonia in methanol solution (100 mL). The eluent was evaporated in vacuo and the residue purified by silica gel chromatography, eluting with 95:5 ethyl acetate:triethylamine to give the subtitled compound as a brown oil. Yield 0.74 g.

후처리

  1. temperaturethen cooled in an ice bath
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 h
  4. washThe cartridge was washed with methanol (100 mL)
  5. washeluted with 3M ammonia in methanol solution (100 mL)
  6. customThe eluent was evaporated in vacuo
  7. customthe residue purified by silica gel chromatography
  8. washeluting with 95:5 ethyl acetate

출처 및 근거

ORD 기록
ord-eb0d4eb9e228495e8a71a519f9a52fef
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

반응 노트

불러오는 중…