Ethyl 3-hydroxy-3-(2-phenylethynyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate → Tert-butyl 4-hydroxy-4-(2-phenylethynyl)-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

HRID 2040859Notes

Reaction equation

HRID 2040859 reaction equation
OC1([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)CC2(CCN(C(OCC)=O)CC2)OC1.[O:25]=[C:26]1[CH2:31][C:30]2([CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]2)[O:29][CH2:28][CH2:27]1>>[OH:25][C:26]1([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:31][C:30]2([CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35][CH2:36]2)[O:29][CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 57493817Ethyl 3-hydroxy-3-(2-phenylethynyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylateHCID 57493827Tert-butyl 4-oxo-1-oxa-9-azaspiro(5.5)undecane-9-carboxylate

Product 1

HCID 57493828Tert-butyl 4-hydroxy-4-(2-phenylethynyl)-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

Procedure

The title compound was prepared following the method reported here for Compound 26a, substituting ethyl 2-oxo-4-oxa-8-azaspiro[4.5]decane-8-carboxylate with Compound 29b. After the usual work-up procedure the oily residue was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc gradient 9:1 to 6:4) to give 0.96 g of the title compound as a grey solid. Yield: 57.3%

Workup

  1. customThe title compound was prepared
  2. customAfter the usual work-up procedure the oily residue was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc gradient 9:1 to 6:4)

Sources & evidence

ORD record
ord-ade1f782d78d436e88da69e181c0e0d0
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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