2-Tert-butyl 1'-(2-adamantyl) 1H-spiro[isoquinoline-4,4'-piperidine]-1',2(3H)-dicarboxylate → 2-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylate

HRID 1424599Notes

Reaction equation

HRID 1424599 reaction equation
[N:1]1([C:23]([O:25][CH:26]2[CH:33]3[CH2:34][CH:29]4[CH2:30][CH:31]([CH2:35][CH:27]2[CH2:28]4)[CH2:32]3)=[O:24])[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:1]1([C:23]([O:25][CH:26]2[CH:27]3[CH2:35][CH:31]4[CH2:30][CH:29]([CH2:34][CH:33]2[CH2:32]4)[CH2:28]3)=[O:24])[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][NH:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 581372792-Tert-butyl 1'-(2-adamantyl) 1H-spiro[isoquinoline-4,4'-piperidine]-1',2(3H)-dicarboxylate

Product 1

HCID 250646132-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylateYield 104.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

2-Tert-butyl 1′-(2-adamantyl) 1H-spiro[isoquinoline-4,4′-piperidine]-1′,2(3H)-dicarboxylate (35 mg, 0.073 mmol) was dissolved in 1:2 TFA/CH2Cl2 (6 mL) and stirred for 30 min at rt. The mixture was concentrated to afford crude 2-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxylate (29 mg, quant). LC-MS Method 1 tR=1.48 min, m/z=381; 1H NMR (CD3OD) δ=7.52 (d, 1H), 7.38 (t, 1H), 7.28 (t, 1H), 7.21 (d, 1H), 4.85 (s, 1H), 4.38 (s, 2H), 4.19 (m, 2H), 3.68 (s, 2H), 3.28-3.01 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-88bdb002311a484686717e2fb407ae62
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…