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 471172

Reaktionsgleichung

Reaktionsgleichung von HRID 471172
[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]

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3cc00e7a348644768a14178472819484
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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