2-Bromopropane → HCID 57968657, compound

HRID 882759Notes

Reaction equation

HRID 882759 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:30]([CH3:32])[CH3:31]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH:30]([CH3:32])[CH3:31])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 44600522HCID 44600522, compound

Product 1

HCID 57968657HCID 57968657, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (287 mg, 0.78 mmol) in DMF (7.8 mL) was added NaH (90%; 31 mg). After 30 min, 2-bromopropane (109 μL, 1.17 mmol) was added and the mixture was allowed to warm to rt and was stirred for 18 h. The mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The crude product was purified by FCC to provide the desired product (26 mg, 8%). MS (ESI): mass calcd. for C22H39N3O4, 409.29; m/z found, 410.4 [M+H]+. 1H NMR (CDCl3): 4.74-4.58 (m, 1H), 4.33-4.16 (m, 1H), 3.74-3.33 (m, 7H), 2.90-2.78 (m, 1H), 2.59-2.30 (m, 4H), 2.19-2.11 (m, 1H), 2.10-1.96 (m, 4H), 1.87-1.72 (m, 3H), 1.69-1.53 (m, 2H), 1.40 (d, J=17.6 Hz, 9H), 1.12 (dd, J=6.0, 2.2 Hz, 6H).

Workup

  1. additionThe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-5e9dcf26c7184798b5266fdf197e4dec
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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