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

HRID 1689184ノート

反応式

HRID 1689184 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 46240301(9-(2-(4-(Hydroxymethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-d212e5ee2f1940f994532992e2387888
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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