[(3,4-Dimethoxyphenyl)methyl]({2-[4-(4-fluorophenyl)-2,2-dimethyloxan-4-yl]ethyl})amine → 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile

HRID 76223Notes

Reaction equation

HRID 76223 reaction equation
COC1C=C(CNCCC2(C3C=CC(F)=CC=3)CCOC(C)(C)C2)C=CC=1OC.[C:30]([CH:32]([C:37]1([C:48]2[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=2)[CH2:42][C:41]2([CH2:47][CH2:46][CH2:45]C[CH2:43]2)[O:40][CH2:39][CH2:38]1)C(OC)=O)#[N:31].C(C(C1(C2C=CC(F)=CC=2)CC2(CCCC2)OCC1)C(OC)=O)#N.FC1C=CC(C2(CC#N)CC3(CCCCC3)OCC2)=CC=1>>[F:54][C:51]1[CH:50]=[CH:49][C:48]([C@@:37]2([CH2:32][C:30]#[N:31])[CH2:42][C:41]3([CH2:43][CH2:45][CH2:46][CH2:47]3)[O:40][CH2:39][CH2:38]2)=[CH:53][CH:52]=1

Participants

5

Reactant 4

HCID 3735781[(3,4-Dimethoxyphenyl)methyl]({2-[4-(4-fluorophenyl)-2,2-dimethyloxan-4-yl]ethyl})amineHCID 68313701Methyl 2-cyano-2-[4-(4-fluorophenyl)-1-oxaspiro[5.5]undecan-4-yl]acetateHCID 68314498HCID 68314498, compoundHCID 683145122-[4-(4-Fluorophenyl)-1-oxaspiro[5.5]undecan-4-yl]acetonitrile

Product 1

HCID 683144862-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile

Procedure

By the procedure described in the preparation of intermediate 10 substituting methyl 2-cyano-2-[4-(4-fluorophenyl)-1-oxaspiro[5.5]undecan-4-yl]acetate for methyl 2-cyano-2-[9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetate, 2-[4-(4-fluorophenyl)-1-oxaspiro[5.5]undecan-4-yl]acetonitrile was prepared (m/z 287.2 [M+H]+ observed).

Workup

  1. customwas prepared (m/z 287.2 [M+H]+ observed)

Sources & evidence

ORD record
ord-e15cb1c8dddc45539463ba8a6eeb1b09
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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