Acetic Acid → 1-(9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

HRID 1689402노트

반응식

HRID 1689402 반응식
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[C:12]([F:19])=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[F:27][C:28]([F:43])([F:42])[C:29]([N:31]1[CH2:36][C:35]2([CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[O:34][CH2:33][CH2:32]1)=[O:30].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.O>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[C:12]([F:19])=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:39]1[CH2:40][CH2:41][C:35]2([O:34][CH2:33][CH2:32][N:31]([C:29](=[O:30])[C:28]([F:27])([F:42])[F:43])[CH2:36]2)[CH2:37][CH2:38]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 579891643-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehydeHCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

생성물 1

HCID 579890151-(9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde (example 78, step b) (2.159 g) was added to stirred solution of 2,2,2-trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (2.80 g) and acetic acid (0.438 mL) in NMP (25 mL). After 5 minutes, sodium triacetoxyborohydride (3.24 g) was added. After 16 h, water was added and the mixture partitioned between water (250 mL) and ethyl acetate (250 mL). The ethyl acetate solution was washed with water (3×250 mL) and brine, then evaporated to dryness. Purification by silica gel chromatography eluting with 20:1:1, isohexane:ethyl acetate:triethylamine gave the subtitled compound as a gum. Yield 2.5 g.

후처리

  1. waitAfter 16 h
  2. customthe mixture partitioned between water (250 mL) and ethyl acetate (250 mL)
  3. washThe ethyl acetate solution was washed with water (3×250 mL) and brine
  4. customevaporated to dryness
  5. customPurification by silica gel chromatography
  6. washeluting with 20:1:1, isohexane

출처 및 근거

ORD 기록
ord-87bc4493b75849a8886921ff1ac9ee3b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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