Hydrochloric Acid → HCID 67356528, compound

HRID 1517207Notes

Reaction equation

HRID 1517207 reaction equation
Cl.[CH2:2]([O:4][CH:5]([O:8][CH2:9][CH3:10])[CH2:6][NH2:7])[CH3:3].[C:11]([Si:15]([CH3:26])([CH3:25])[O:16][C@H:17]1[CH2:21][C:20](OCC)=[N:19][CH2:18]1)([CH3:14])([CH3:13])[CH3:12]>C(O)C>[C:11]([Si:15]([CH3:26])([CH3:25])[O:16][C@@H:17]1[CH2:18][N:19]=[C:20]([NH:7][CH2:6][CH:5]([O:8][CH2:9][CH3:10])[O:4][CH2:2][CH3:3])[CH2:21]1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 695242,2-DiethoxyethylamineHCID 68510373HCID 68510373, compound

Product 1

HCID 67356528HCID 67356528, compoundYield 434.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanolic hydrogen chloride (1M, 420 mL) was added dropwise to a solution of aminoacetaldehyde diethyl acetal (55.1 g, 0.14 mol) and the compound isolated in Step 2 (101 g, 0.41 mol) in ethanol (1500 mL). This mixture was stirred at room temperature for 16 hours, and then evaporated under reduced pressure. The resulting solid was recrystalised from ether to give [(S)-4-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydro-3H-pyrrol-2-yl]-(2,2-diethoxy-ethyl)-amine as a solid (201 g, 78%).

Workup

  1. customevaporated under reduced pressure
  2. customThe resulting solid was recrystalised from ether

Sources & evidence

ORD record
ord-3a5c68d1775641aca84033ab8c9ecfba
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

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