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

HRID 470953노트

반응식

HRID 470953 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][C:23]1[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH:29]=O)=[CH:25][CH:24]=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][C:23]1[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH2:29][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:25][CH:24]=1

참가 물질

7

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 544756782-(4-(Hydroxymethyl)phenoxy)acetaldehydeHCID 67291637(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride

생성물 1

HCID 46240301(9-(2-(4-(Hydroxymethyl)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) (0.38 g) was added to a solution of 2-(4-(hydroxymethyl)phenoxy)acetaldehyde (example 1, step h) (0.17 g) in NMP (10 mL) and acetic acid (0.06 mL). The resulting mixture was stirred for 30 min then cooled in an ice bath. Sodium triacetoxyborohydride (0.32 g) was then added and the reaction 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 (250 mL) and eluted with 3M ammonia in methanol solution (150 mL). The eluent was evaporated in vacuo and the residue purified by column chromatography eluting with 95:5 ethyl acetate:triethylamine to give the subtitled compound as a gum. Yield 0.32 g.

후처리

  1. temperaturethen cooled in an ice bath
  2. stirringstirred for 16 h
  3. washThe cartridge was washed with methanol (250 mL)
  4. washeluted with 3M ammonia in methanol solution (150 mL)
  5. customThe eluent was evaporated in vacuo
  6. customthe residue purified by column chromatography
  7. washeluting with 95:5 ethyl acetate

출처 및 근거

ORD 기록
ord-1fe01b4243f24ca7b02910407c4d5b4f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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