Aluminium lithium hydride → HCID 46231721, compound

HRID 1424637Notes

Reaction equation

HRID 1424637 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](=[O:27])[NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:29][C:30](OCC)=[O:31].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[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]([NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[O:27])[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH2:29][CH2:30][OH:31]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 25064817HCID 25064817, compound

Product 1

HCID 46231721HCID 46231721, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-ethyl 2-(7-bromo-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (300 mg, 0.566 mmol) in THF (5 mL) was added LiAlH4 (65 mg, 1.132 mmol) at 0° C. under N2. The mixture was stirred overnight at rt. The mixture was separated by preparative TLC to give the crude product, which was purified by preparative HPLC to afford (±)-7-bromo-N-(2-adamantyl)-3-(2-hydroxyethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (26 mg, 10%). LC-MS Method 5 tR=1.467 min, m/z=489.1; 1H NMR: (400 MHz, CDCl3): δ=1.38 (m, 2H), 1.62 (m. 5H), 1.71 (m, 5H), 1.75-1.88 (m, 9H), 2.19 (m, 2H), 2.21-2.49 (m, 5H), 2.52 (m, 1H), 2.95-3.12 (m, 3H), 3.21 (m, 1H), 3.78 (m, 2H), 3.82 (m, 3H), 7.03 (m, 1H), 7.08 (m, 1H), 7.32 (m, 1H).

Workup

  1. customThe mixture was separated by preparative TLC
  2. customto give the crude product, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f97c152f3fc3466ba00a1bfd444d429c
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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