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Diisopropylethylamine → HCID 58171517, compound

HRID 1752313
Notes
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Reaction equation

HRID 1752313 reaction equation
Cl.[C:2]1([C:8]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH:31]1[CH:38]2[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:40][CH:32]1[CH2:33]3)[CH2:37]2)=[O:29]>C(Cl)Cl.CCOCC>[C:2]1([C:8]2([C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:10][N:11]([C:28]([O:30][CH:31]3[CH:32]4[CH2:40][CH:36]5[CH2:35][CH:34]([CH2:39][CH:38]3[CH2:37]5)[CH2:33]4)=[O:29])[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3019446Methyl 4-phenylpiperidine-4-carboxylate hydrochlorideHCID 108785372-adamantyl Chloroformate

Product 1

HCID 58171517HCID 58171517, compoundYield 2.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred, ice-cold solution of methyl 4-phenylpiperidine-4-carboxylate hydrochloride (983 mg, 3.8 mmol) and i-Pr2NEt (1.88 mL, 10.5 mmol) in CH2Cl2 (25 mL) was added 2-adamantyl chloroformate (750 mg, 3.5 mmol). The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (150 mL), washed with 5% aq HCl (2×30 mL) and satd aq NaHCO3 (30 mL) and dried over MgSO4. Removal of the solvent left the crude product (1.37 g, 99%) as a white solid. A 40-mg portion was purified by prep HPLC to afford the title compound (32 mg). LC-MS Method 1 tR=2.4 min, m/z=398, 1H NMR (CDCl3) 1.58 (m, 2H), 1.70-2.10 (14H), 2.56 (d, 2H), 3.10 (br d, 2H), 3.68 (s, 3H), 4.08 (d, 2H), 4.83 (s, 1H), 7.27 (m, 1H), 7.36 (m, 4H).

Workup

  1. washwashed with 5% aq HCl (2×30 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. waitleft the crude product (1.37 g, 99%) as a white solid
  5. customA 40-mg portion was purified by prep HPLC

Sources & evidence

ORD record
ord-10f5305a8a5941a69c6adb635daaed01
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09163012B2

Reaction notes

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