Dichloromethane → HCID 18648615, compound

HRID 1590363Notes

Reaction equation

C(OC([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:34]>>[ClH:34].[NH2:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1

Participants

Reactant 3

HCID 6344Dichloromethane2×

HCID 6422Trifluoroacetic acid

HCID 10427899HCID 10427899, compound

Product 1

HCID 18648615HCID 18648615, compound

Procedure

A solution of 1 g of (S)-2-[N-(tert-butoxycarbonyl)amino]-7-carbethoxymethoxytetraline, EXAMPLE 5, in 15 ml of methylene chloride is cooled to 0° C. A solution of 2.2 ml of trifluoroacetic acid in 15 ml of methylene chloride is added thereto and the reacting mixture is left under stirring 30 minutes at a temperature of 0°-5° C. and afterwards 4 hours at room temperature. By operating as described in EXAMPLE 4, the (S)-2-amino-7-carbethoxymethoxytetraline hydrochloride is obtained; /alpha/=-52° (methanol, c=1%). The product so obtained may be used for the preparation of N-[(2S)-7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl]-(2R)-2-hydroxy-2-phenylethanamine R,S isomer of COMPOUND 1) as follows:

Workup

waitthe reacting mixture is left

Sources & evidence

ORD record: ord-41483fea5c2642778d04d4d9cf4cfb3b
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202466

Reaction notes

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