Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

HRID 470979Notes

Reaction equation

HRID 470979 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O.[CH3:19][C:20]1[S:24][C:23]([C:25]([N:27]2[CH2:32][C:31]3([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[O:30][CH2:29][CH2:28]2)=[O:26])=[CH:22][CH:21]=1.C(N(CC)CC)C>CC#N>[OH:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:35]1[CH2:36][CH2:37][C:31]2([O:30][CH2:29][CH2:28][N:27]([C:25]([C:23]3[S:24][C:20]([CH3:19])=[CH:21][CH:22]=3)=[O:26])[CH2:32]2)[CH2:33][CH2:34]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292300(5-Methylthiophen-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Product 1

HCID 46240297(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(3-(Bromomethyl)phenyl)ethanol (example 6, step a) (0.136 g) was added to a stirred solution of (5-methylthiophen-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 9, step b) (0.250 g) and triethylamine (0.278 mL) in MeCN (5 mL). After 1 h, the reaction mixture was concentrated and applied to a silica gel column eluting with ethyl acetate:triethylamine, 95:5 to give the subtitled compound. Yield 0.24 g.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ea267c8f0dd94de08ae7d99ed4229600
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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