Triethylamine → methyl N-(decahydro-1-naphthalenyl)glycine

HRID 621385Notes

Reaction equation

HRID 621385 reaction equation
[CH:1]1([NH2:11])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[CH2:12](N(CC)CC)C.Br[CH2:20][C:21]([O:23]C)=[O:22]>CCCCCC>[CH3:12][N:11]([CH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1)[CH2:20][C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 232603Decahydronaphthalen-1-amine

Product 1

HCID 70377605methyl N-(decahydro-1-naphthalenyl)glycine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 203 parts of decahydro-1-naphthalenamine and 161 parts of N,N-diethylethanamine in 40 parts of hexane were added dropwise 122 parts of methyl bromoacetate. Upon complete addition, stirring was continued for 24 hours at room temperature. The precipitate was filtered off and the filtrate was concentrated to dry, yielding methyl N-(decahydro-1-naphthalenyl)glycine (intermediate 5).

Workup

  1. additionUpon complete addition
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customto dry

Sources & evidence

ORD record
ord-7d484f8976f946ccb54553b25341cb54
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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