1,2-Dichloroethane → HCID 68291716, compound

HRID 73013Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:18][CH2:17][C:16]3([CH2:23][NH:22][CH2:21][CH:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:19]3)[CH2:15][CH2:14]2)=[O:12])=[CH:7][C:6]=1[CH3:30])([CH3:3])[CH3:2].[CH3:31][C:32]([CH3:34])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:49]CCCl>>[ClH:49].[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:14][CH2:15][C:16]3([CH2:23][N:22]([CH:32]([CH3:34])[CH3:31])[CH2:21][CH:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:19]3)[CH2:17][CH2:18]2)=[O:12])=[CH:7][C:6]=1[CH3:30])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 180Acetone

HCID 5049666Sodium triacetoxyborohydride

HCID 68291585HCID 68291585, compound

Product 1

HCID 68291716HCID 68291716, compoundYield 36%

Procedure

To (4-isopropoxy-3-methyl-phenyl)-(8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)methanone (30 mg, 0.07 mmol) and acetone (130 μL, 1.77 mmol) in DCE (0.5 mL) was added sodium triacetoxyborohydride (50 mg, 0.24 mmol) and the reaction mixture was stirred for 5 hours. The reaction mixture was concentrated in vacuo, diluted with methanol, microfiltered and purified by preparative LCMS (1-99% ACN/H2O, 5 mM HCl modifier) to give (4-isopropoxy-3-methyl-phenyl)-(10-isopropyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)methanone hydrochloride salt (13 mg, 36%) as a glassy solid. ESI-MS m/z calc. 450.2. Found 451.5 (M+1)+; Retention time: 1.38 minutes (3 min run).

Workup

concentrationThe reaction mixture was concentrated in vacuo
additiondiluted with methanol
custommicrofiltered and purified by preparative LCMS (1-99% ACN/H2O, 5 mM HCl modifier)

Sources & evidence

ORD record: ord-b3e1613c962e4c46a4de84b515e61f62
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828996B2

Reaction notes

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