Hydrochloric Acid → HCID 25066064, compound

HRID 1424624Notes

Reaction equation

HRID 1424624 reaction equation
Cl.[CH2:2]1[C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3]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].Cl>C(Cl)Cl>[CH3:17][O:16][C:14](=[O:15])[CH2:13][CH:10]1[CH2:11][CH2:12][C:7]2([CH2:2][CH2:3][N:4]([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])[CH2:5][CH2:6]2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 108785372-adamantyl ChloroformateHCID 66954296HCID 66954296, compound

Product 1

HCID 25066064HCID 25066064, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial was charged with methyl 2-(3-azaspiro[5.5]undecan-9-yl)acetate HCl salt (31 mg, 0.12 mmol) and DIEA (45 μL, 0.25 mmol). A solution of 2-adamantyl chloroformate (25 mg, 0.12 mmol) in CH2Cl2 (2 mL) was added and the mixture was stirred overnight at rt. A 10-mL Chem-Elut cartridge was wetted with 5% aq HCl (6 mL) and allowed to stand for 5 min. The reaction mixture was applied to the cartridge and eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford (2-adamantyl) 9-(2-methoxy-2-oxoethyl)-3-azaspiro[5.5]undecane-3-carboxylate (35 mg, 74%). LC-MS Method 1 tR=2.52 min, m/z=404; 1H NMR (CDCl3) δ=1.05-2.10 (27H), 2.23 (d, 2H), 3.41 (m, 4H), 3.69 (s, 3H), 4.82 (s, 1H).

Workup

  1. waitto stand for 5 min
  2. washeluted with ether (20 mL)
  3. customThe eluate was evaporated to dryness
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b6f9c51b0852480497652a23bcc80c7f
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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