Water → trans-1-(2-Hydroxymethylanilino)-2-methylaminoindane

HRID 980509Notes

Reaction equation

HRID 980509 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][CH:24]=[CH:23][C:6]=1[NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[NH:17][C:18](OCC)=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[OH:2][CH2:3][C:5]1[CH:26]=[CH:25][CH:24]=[CH:23][C:6]=1[NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[NH:17][CH3:18]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 54064549trans-1-(2-Methoxycarbonylanilino)-2-ethoxycarbonylaminoindane

Product 1

HCID 15807945trans-1-(2-Hydroxymethylanilino)-2-methylaminoindaneYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of trans 1-(2-methoxycarbonylanilino)-2-ethoxycarbonylaminoindane (1.73 kg; 4.9 moles) in diethyl ether (36 l) was added dropwise to a suspension of lithium aluminum hydride (900 g; 23.7 moles) in diethyl ether (28 l), under nitrogen, over a period of ca 1.5 h. After stirring overnight at room temperature the excess lithium aluminium hydride was carefully decomposed with water (2.5 l), and 10% sodium hydroxide (30 l) and water (5 l) was added. The organic layer was separated and the aqueous phase extracted with two further portions of ether (2×20 l). The combined extracts were washed (water), dried (MgSO4) and concentrated. Crystallisation from ethyl acetate/pet. ether afforded the title compound (1.17 Kg; 89%) m.p. 113°-4°.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with two further portions of ether (2×20 l)
  4. washThe combined extracts were washed (water)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customCrystallisation from ethyl acetate/pet. ether

Sources & evidence

ORD record
ord-75b9dcda7bf545f78b7fa8700713f672
Source dataset
uspto-grants-1987_01
Patent number
US04638066

Reaction notes

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