Potassium Hydroxide → 1-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene

HRID 1741415

Reaction equation

HRID 1741415 reaction equation
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][CH:24]2[NH2:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([C:49](=O)[CH2:50][CH2:51][CH:52]=O)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:33][CH:32]=1.[BH3-]C#N.[Na+].[OH-].[K+]>C(O)(=O)C.CO>[CH3:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:38]=[C:39]([CH:49]3[CH2:50][CH2:51][CH2:52][N:29]3[CH:24]3[C:25]4[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:22][CH2:23]3)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 183672311,2,3,4-Tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamineHCID 183673471-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione

Product 1

HCID 183672421-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthaleneYield 94.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamine (0.21 g), 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.12 g), NaBH3CN (84 mg) and KOH (30 mg) in acetic acid (0.5 ml) and methanol (4 ml). After being stirred for 3 days at room temperature, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[2-[4,5-bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene (0.24 g). FABMS (m/z): 702 (M+ -1) NMR (CDCl3, δ): 1.08 (9H, s), 1.58-3.04 (12H, m), 2.34 (3H, s), 2.36 (3H, s), 6.18-7.80 (21H, m)

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and sat. NaHCO3
  3. washThe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f18da2ce4fbe40ddb55e49c0bac305d2
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Linked notes

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