1-Bromopropane → HCID 69676465, compound

HRID 919585Notes

Reaction equation

HRID 919585 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Br[CH2:16][CH2:17][CH3:18].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:16]([NH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylate

Product 1

HCID 69676465HCID 69676465, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-tert-butyl 3-aminopiperidine-1-carboxylate (500 mg, 2.49 mmol) and 1-bromopropane (335 mg, 2.74 mmol) and DIEA (0.11 mL, 6.24 mmol) in DMF (4 mL) was heated at 100° C. for overnight. After reaction was shown to be complete as indicated by TLC, the mixture was diluted with EtOAc (30 mL) and washed with water (2×15 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo to afford a residue which was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to yield the titled intermediate (605 mg, 57%). 1H NMR (400 MHz, DMSO-d6): δ 3.89-3.64 (m, 3H), 2.80-2.66 (m, 2H), 2.50-2.35 (m, 3H), 1.89-1.83 (m, 2H), 1.61-1.58 (m, 2H), 1.38 (s, 9H), 1.35-1.29 9m, 2H), 0.82 (t, J=7.2 Hz, 3H). ES-MS: m/z [M+1]=243.

Workup

  1. customAfter reaction
  2. washwashed with water (2×15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford a residue which
  7. customwas purified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1dc94bb71df549e09ca9051213a8c8a5
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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