Acetone → HCID 66953455, compound

HRID 1424617Notes

Reaction equation

HRID 1424617 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15]([NH:17][CH:18]3[CH:25]4[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)=[O:16])[CH2:11][CH2:10]1)[CH2:8][CH:7]2[C:29]([CH3:33])([CH3:32])[CH:30]=[O:31].CC(C)=[O:36]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:10][CH2:11][N:12]([C:15](=[O:16])[NH:17][CH:18]3[CH:25]4[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)[CH2:13][CH2:14]1)[CH2:8][CH:7]2[C:29]([CH3:33])([CH3:32])[C:30]([OH:36])=[O:31]

Participants

3

Reactant 2

HCID 180AcetoneHCID 86650840HCID 86650840, compound

Product 1

HCID 66953455HCID 66953455, compoundYield 5%

Procedure

To a solution of crude (±)-7-bromo-N-(2-adamantyl)-3-(2-methyl-1-oxopropan-2-yl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (40 mg, 0.0778 mmol) in dry acetone was added H2Cr2O7 (234 mg, 0.8 mmol), and the solution was stirred for 1 h. 0.5 Treatment of the mixture with NaBH4 and concentration afforded the crude product which was purified by preparative HPLC to give (±)-2-(7-bromo-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)-2-methylpropanoic acid (1.55 mg, 5%). LC-MS Method 5 tR=1.504 min, m/z=531; 1H NMR: (400 MHz, CDCl3): δ=1.04 (s, 3H), 1.21 (s, 3H), 1.34-1.43 (m, 2H), 1.60-1.71 (m, 3H), 1.76-2.08 (m, 13H), 2.29-2.40 (m, 1H), 2.51-2.61 (m, 1H), 2.99-3.27 (m, 3H), 3.89 (m, 2H), 4.02-4.14 (m; 2H), 7.01 (m, 1H), 7.21-7.33 (m, 2H).

Workup

  1. concentration0.5 Treatment of the mixture with NaBH4 and concentration
  2. customafforded the crude product which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f4b647e6d4344a86851c28b5cc6c859d
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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