Hydrogen Bromide → HCID 58010084, compound

HRID 2204520Notes

Reaction equation

HRID 2204520 reaction equation
Cl[C:2]([C@@H:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:5]1)=[O:3].[CH3:27][Si](C=[N+]=[N-])(C)C.C1COCC1.CC#N.[BrH:42]>C1COCC1.CC#N>[Br:42][CH2:27][C:2]([C@@H:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:5]1)=[O:3]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 22177404Acetonitrile tetrahydrofuranHCID 58010181HCID 58010181, compound

Product 1

HCID 58010084HCID 58010084, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-(9H-fluoren-9-yl)methyl 3-(chlorocarbonyl)piperidine-1-carboxylate (4.21 g, 11.4 mmol, prepared using W from (R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid [Fluka]) was dissolved in a mixture of THF and MeCN (1:1, 16 mL) and added to a solution of trimethylsilyldiazomethane (2 M in Et2O, 22.8 mL, 45.5 mmol) and THF/MeCN (1:1, 16 mL) at about 0° C. The resulting mixture was stirred at about 0° C. for about 4 h followed by the drop-wise addition of HBr (48% aqueous solution, 6.2 mL, 114 mmol). The organic solvents were removed and the precipitate was collected by filtration and dried in air to give (R)-(9H-fluoren-9-yl)methyl 3-(2-bromoacetyl)piperidine-1-carboxylate (4.46 g, 92%): LC/MS (Table 2, Method a) Rt=2.59 min; MS m/z: 428/430 (M+H)+.

Workup

  1. customThe organic solvents were removed
  2. filtrationthe precipitate was collected by filtration
  3. customdried in air

Sources & evidence

ORD record
ord-4b1c0b8eabcd4aa189523d7c22d7ecd3
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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