Tetrahydrofuran → (S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one

HRID 2299890Notes

Reaction equation

HRID 2299890 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C([N:32]([CH2:36][CH3:37])C(C)C)(C)C.Br[CH2:39][CH:40]=[C:41]([CH3:43])[CH3:42].[CH2:44]1[CH2:48]OC[CH2:45]1>>[NH2:32][C@@H:36]([CH2:37][CH:44]([CH3:48])[CH3:45])[C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:17][CH:16]=2)[CH2:39][CH:40]=[C:41]([CH3:43])[CH3:42])[CH2:12][CH2:13]1)=[O:7]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 700922-Butene, 1-bromo-3-methyl-HCID 81531DiisopropylethylamineHCID 105479494-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 10004622(S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-oneYield 87%

Conditions

Temperature
40 °C

Procedure

4-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 13.1 mmol) was dissolved in THF (65 mL), then treated with N,N-diisopropylethylamine (9.1 mL, 52.4 mmol) and 4-bromo-2-methyl-2-butene (3.0 mL, 26.2 mmol). The reaction was heated to 40° C. for 18 hours, then concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5:1 hexane/EtOAc to give 5.15 g (87%) of the desired compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with 5:1 hexane/EtOAc

Sources & evidence

ORD record
ord-08e9d8ca88654e33b6b295cb6fe270ec
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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